Synthesis, and QSAR analysis of anti-oncological active spiro-alkaloids

Siva S Panda

doi:10.1039/c4ob02149e

Synthesis, and QSAR analysis of anti-oncological active spiro-alkaloids

Siva S Panda

Chemistry and Biochemistry

Research output: Contribution to journal › Article › peer-review

37 Scopus citations

Abstract

QSAR study describes the anti-neoplastic spiro-alkaloids with relevant molecular descriptors using CODESSA III software. The dispiro[3H-indole-3,2'-pyrrolidine-3',3"-piperidines] 24-48 were synthesized via [3 + 2]-cycloaddition reaction of azomethine ylides, (generated in situ via decarboxylative condensation of isatins 21-23 with sarcosine) and 3E,5E-1-alkyl-3,5-bis(arylmethylidene)-4-piperidones 10-20. Some of the synthesized analogues exhibited promising antitumor properties against HELA (cervical), HEPG2 (liver), T-47D, MCF7 (breast), and HCT116 (colon) human tumor cell lines, demonstrating activity close to or even better than the standard Doxorubicin, based on in vitro Sulfo-Rhodamine-B bio-assay.

Original language	English (US)
Pages (from-to)	1741-53
Number of pages	13
Journal	Organic and Biomolecular Chemistry
Volume	13
Issue number	6
DOIs	https://doi.org/10.1039/c4ob02149e
State	Published - Feb 14 2015

Keywords

Alkaloids
Antineoplastic Agents
Cell Line, Tumor
Cell Proliferation
Dose-Response Relationship, Drug
Drug Screening Assays, Antitumor
Humans
Models, Molecular
Molecular Structure
Quantitative Structure-Activity Relationship
Software
Spiro Compounds
Journal Article
Research Support, Non-U.S. Gov't

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10.1039/c4ob02149e

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title = "Synthesis, and QSAR analysis of anti-oncological active spiro-alkaloids",

abstract = "QSAR study describes the anti-neoplastic spiro-alkaloids with relevant molecular descriptors using CODESSA III software. The dispiro[3H-indole-3,2'-pyrrolidine-3',3{"}-piperidines] 24-48 were synthesized via [3 + 2]-cycloaddition reaction of azomethine ylides, (generated in situ via decarboxylative condensation of isatins 21-23 with sarcosine) and 3E,5E-1-alkyl-3,5-bis(arylmethylidene)-4-piperidones 10-20. Some of the synthesized analogues exhibited promising antitumor properties against HELA (cervical), HEPG2 (liver), T-47D, MCF7 (breast), and HCT116 (colon) human tumor cell lines, demonstrating activity close to or even better than the standard Doxorubicin, based on in vitro Sulfo-Rhodamine-B bio-assay.",

keywords = "Alkaloids, Antineoplastic Agents, Cell Line, Tumor, Cell Proliferation, Dose-Response Relationship, Drug, Drug Screening Assays, Antitumor, Humans, Models, Molecular, Molecular Structure, Quantitative Structure-Activity Relationship, Software, Spiro Compounds, Journal Article, Research Support, Non-U.S. Gov't",

author = "Panda, {Siva S}",

year = "2015",

month = feb,

day = "14",

doi = "10.1039/c4ob02149e",

language = "English (US)",

volume = "13",

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journal = "Organic and Biomolecular Chemistry",

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publisher = "Royal Society of Chemistry",

number = "6",

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T1 - Synthesis, and QSAR analysis of anti-oncological active spiro-alkaloids

AU - Panda, Siva S

PY - 2015/2/14

Y1 - 2015/2/14

N2 - QSAR study describes the anti-neoplastic spiro-alkaloids with relevant molecular descriptors using CODESSA III software. The dispiro[3H-indole-3,2'-pyrrolidine-3',3"-piperidines] 24-48 were synthesized via [3 + 2]-cycloaddition reaction of azomethine ylides, (generated in situ via decarboxylative condensation of isatins 21-23 with sarcosine) and 3E,5E-1-alkyl-3,5-bis(arylmethylidene)-4-piperidones 10-20. Some of the synthesized analogues exhibited promising antitumor properties against HELA (cervical), HEPG2 (liver), T-47D, MCF7 (breast), and HCT116 (colon) human tumor cell lines, demonstrating activity close to or even better than the standard Doxorubicin, based on in vitro Sulfo-Rhodamine-B bio-assay.

AB - QSAR study describes the anti-neoplastic spiro-alkaloids with relevant molecular descriptors using CODESSA III software. The dispiro[3H-indole-3,2'-pyrrolidine-3',3"-piperidines] 24-48 were synthesized via [3 + 2]-cycloaddition reaction of azomethine ylides, (generated in situ via decarboxylative condensation of isatins 21-23 with sarcosine) and 3E,5E-1-alkyl-3,5-bis(arylmethylidene)-4-piperidones 10-20. Some of the synthesized analogues exhibited promising antitumor properties against HELA (cervical), HEPG2 (liver), T-47D, MCF7 (breast), and HCT116 (colon) human tumor cell lines, demonstrating activity close to or even better than the standard Doxorubicin, based on in vitro Sulfo-Rhodamine-B bio-assay.

KW - Alkaloids

KW - Antineoplastic Agents

KW - Cell Line, Tumor

KW - Cell Proliferation

KW - Dose-Response Relationship, Drug

KW - Drug Screening Assays, Antitumor

KW - Humans

KW - Models, Molecular

KW - Molecular Structure

KW - Quantitative Structure-Activity Relationship

KW - Software

KW - Spiro Compounds

KW - Journal Article

KW - Research Support, Non-U.S. Gov't

U2 - 10.1039/c4ob02149e

DO - 10.1039/c4ob02149e

M3 - Article

C2 - 25502495

SN - 1477-0520

VL - 13

SP - 1741

EP - 1753

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 6

ER -

Synthesis, and QSAR analysis of anti-oncological active spiro-alkaloids

Abstract

Keywords

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